NPASS Compound

Structure

CID117137 OpenBabel06191715472D 26 30 0 0 1 0 0 0 0 0999 V2000 -1.1923 -0.8559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9215 -0.1993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5858 -1.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0489 2.0864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8943 1.0123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9193 1.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4328 -1.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9860 -1.0277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3523 0.1303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1612 0.5618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4578 -0.8821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3343 1.5728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4042 0.9079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1761 0.2164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1949 1.0759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9883 0.1039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9479 -0.7777 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3660 1.1579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1909 -0.4315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1308 -1.6672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0511 0.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9028 -0.5295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0116 1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6848 -0.7028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1949 2.0697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 1 0 0 0 10 18 1 6 0 0 0 10 19 1 0 0 0 0 11 20 1 1 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 12 26 1 1 0 0 0 13 18 1 1 0 0 0 13 20 1 0 0 0 0 14 19 1 6 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 1 0 0 0 16 20 1 0 0 0 0 17 3 1 1 0 0 0 17 23 1 0 0 0 0 18 4 1 1 0 0 0 18 24 1 0 0 0 0 19 7 1 6 0 0 0 20 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.22
Volume:	364.435
LogP:	1.238
LogD:	0.461
LogS:	-3.535
# Rotatable Bonds:	0
TPSA:	113.68
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	6.52
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.48
MDCK Permeability:	5.788926500827074e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.678
Human Intestinal Absorption (HIA):	0.76
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	44.6860237121582%
Volume Distribution (VD):	0.843
Pgp-substrate:	40.18511199951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.627
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.153
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	1.69
Half-life (T1/2):	0.674

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.347
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.316
Carcinogencity:	0.021
Eye Corrosion:	0.011
Eye Irritation:	0.107
Respiratory Toxicity:	0.968

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC117137

Natural Product ID:	NPC117137
*Common Name:**	VUMZHZYKXUYIHM-GLHQSWFFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VUMZHZYKXUYIHM-GLHQSWFFSA-N
Standard InCHI:	InChI=1S/C20H32O6/c1-16(2)15-12(26-15)13-18(4,24)10-6-5-9-14(22)19(10,8-17(9,3)23)7-11(21)20(13,16)25/h9-15,21-25H,5-8H2,1-4H3/t9-,10+,11-,12+,13+,14-,15+,17-,18-,19+,20-/m1/s1
SMILES:	CC1(C)[C@@H]2[C@H]([C@H]3[C@@](C)([C@@H]4CC[C@@H]5[C@H]([C@@]4(C[C@H]([C@]13O)O)C[C@@]5(C)O)O)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3763486
PubChem CID:	21151017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002871] Grayanoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	flowers	n.a.	n.a.	PMID[15974620]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[26599832]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29272126]
NPO25878	Rhododendron japonicum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25878	Rhododendron japonicum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25878	Rhododendron japonicum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
LD50	1
Others	7

Activity Type	# Activity
Cell Line	4
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	>	50.0	%	PMID[489278]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7000.0	nM	PMID[489278]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	96.5	%	PMID[489278]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	98.4	%	PMID[489278]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	0.271	mg.kg-1	PMID[489277]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.0469	mg.kg-1	PMID[489277]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	73.7	%	PMID[489277]
NPT32	Organism	Mus musculus	Mus musculus	Selectivity Index	=	5.8	n.a.	PMID[489277]
NPT32	Organism	Mus musculus	Mus musculus	FC	=	100.0	n.a.	PMID[489277]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC117137 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	481
0.1-0.2	5129
0.2-0.3	16649
0.3-0.4	8402
0.4-0.5	6564
0.5-0.6	4420
0.6-0.7	872
0.7-0.8	137
0.8-0.85	19
0.85-0.9	13
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC66766
0.9324	High Similarity	NPC131584
0.9324	High Similarity	NPC139765
0.9114	High Similarity	NPC29342
0.9114	High Similarity	NPC2572
0.9012	High Similarity	NPC64862
0.8861	High Similarity	NPC473257
0.8415	Intermediate Similarity	NPC69953
0.8375	Intermediate Similarity	NPC269333
0.8354	Intermediate Similarity	NPC476233
0.8353	Intermediate Similarity	NPC22376
0.8313	Intermediate Similarity	NPC242016
0.8293	Intermediate Similarity	NPC475388
0.8235	Intermediate Similarity	NPC5943
0.8205	Intermediate Similarity	NPC475458
0.8118	Intermediate Similarity	NPC145245
0.8118	Intermediate Similarity	NPC131365
0.8101	Intermediate Similarity	NPC317242
0.8101	Intermediate Similarity	NPC472950
0.8101	Intermediate Similarity	NPC472952
0.809	Intermediate Similarity	NPC39453
0.8049	Intermediate Similarity	NPC16449
0.8023	Intermediate Similarity	NPC472396
0.8	Intermediate Similarity	NPC470145
0.8	Intermediate Similarity	NPC163597
0.7927	Intermediate Similarity	NPC477282
0.7927	Intermediate Similarity	NPC287452
0.7927	Intermediate Similarity	NPC81074
0.7901	Intermediate Similarity	NPC474574
0.7901	Intermediate Similarity	NPC133596
0.7901	Intermediate Similarity	NPC105208
0.7901	Intermediate Similarity	NPC185915
0.7901	Intermediate Similarity	NPC128951
0.7901	Intermediate Similarity	NPC302578
0.7901	Intermediate Similarity	NPC477227
0.7901	Intermediate Similarity	NPC192046
0.7901	Intermediate Similarity	NPC11907
0.7901	Intermediate Similarity	NPC64081
0.7882	Intermediate Similarity	NPC474156
0.7867	Intermediate Similarity	NPC165069
0.7848	Intermediate Similarity	NPC153719
0.7848	Intermediate Similarity	NPC470610
0.7831	Intermediate Similarity	NPC474714
0.7816	Intermediate Similarity	NPC210658
0.7816	Intermediate Similarity	NPC161928
0.7805	Intermediate Similarity	NPC67657
0.7805	Intermediate Similarity	NPC18857
0.7805	Intermediate Similarity	NPC471769
0.7791	Intermediate Similarity	NPC266651
0.775	Intermediate Similarity	NPC304499
0.775	Intermediate Similarity	NPC48795
0.7733	Intermediate Similarity	NPC199937
0.7727	Intermediate Similarity	NPC128475
0.7722	Intermediate Similarity	NPC187471
0.7722	Intermediate Similarity	NPC1340
0.7722	Intermediate Similarity	NPC252182
0.7722	Intermediate Similarity	NPC470071
0.7701	Intermediate Similarity	NPC471240
0.7692	Intermediate Similarity	NPC30687
0.7674	Intermediate Similarity	NPC320824
0.7667	Intermediate Similarity	NPC473066
0.7667	Intermediate Similarity	NPC59006
0.7654	Intermediate Similarity	NPC231680
0.7654	Intermediate Similarity	NPC196136
0.7654	Intermediate Similarity	NPC270306
0.7654	Intermediate Similarity	NPC243027
0.7654	Intermediate Similarity	NPC158208
0.7654	Intermediate Similarity	NPC91387
0.7647	Intermediate Similarity	NPC470611
0.764	Intermediate Similarity	NPC228059
0.7632	Intermediate Similarity	NPC472946
0.7619	Intermediate Similarity	NPC472943
0.7619	Intermediate Similarity	NPC472951
0.7595	Intermediate Similarity	NPC251201
0.7595	Intermediate Similarity	NPC232925
0.7595	Intermediate Similarity	NPC63588
0.759	Intermediate Similarity	NPC147993
0.759	Intermediate Similarity	NPC471045
0.7586	Intermediate Similarity	NPC232044
0.7586	Intermediate Similarity	NPC273290
0.7564	Intermediate Similarity	NPC474756
0.7558	Intermediate Similarity	NPC470070
0.7531	Intermediate Similarity	NPC228994
0.7531	Intermediate Similarity	NPC192501
0.7531	Intermediate Similarity	NPC10476
0.75	Intermediate Similarity	NPC157777
0.75	Intermediate Similarity	NPC127283
0.75	Intermediate Similarity	NPC155531
0.75	Intermediate Similarity	NPC215968
0.75	Intermediate Similarity	NPC131506
0.75	Intermediate Similarity	NPC470424
0.75	Intermediate Similarity	NPC8004
0.75	Intermediate Similarity	NPC476176
0.75	Intermediate Similarity	NPC175
0.7471	Intermediate Similarity	NPC227260
0.747	Intermediate Similarity	NPC188793
0.7468	Intermediate Similarity	NPC477820
0.7468	Intermediate Similarity	NPC66407
0.7468	Intermediate Similarity	NPC107919
0.7444	Intermediate Similarity	NPC20822
0.7442	Intermediate Similarity	NPC60018
0.7442	Intermediate Similarity	NPC296734
0.7442	Intermediate Similarity	NPC202688
0.7442	Intermediate Similarity	NPC154043
0.7436	Intermediate Similarity	NPC63190
0.7419	Intermediate Similarity	NPC473065
0.7419	Intermediate Similarity	NPC473067
0.7419	Intermediate Similarity	NPC473064
0.7391	Intermediate Similarity	NPC182740
0.7391	Intermediate Similarity	NPC211845
0.7391	Intermediate Similarity	NPC122083
0.7391	Intermediate Similarity	NPC167644
0.7391	Intermediate Similarity	NPC256104
0.7391	Intermediate Similarity	NPC311246
0.7386	Intermediate Similarity	NPC290612
0.7363	Intermediate Similarity	NPC279329
0.7363	Intermediate Similarity	NPC473542
0.7356	Intermediate Similarity	NPC477285
0.7356	Intermediate Similarity	NPC478054
0.7356	Intermediate Similarity	NPC111582
0.734	Intermediate Similarity	NPC156377
0.734	Intermediate Similarity	NPC142264
0.734	Intermediate Similarity	NPC476510
0.7333	Intermediate Similarity	NPC281004
0.7317	Intermediate Similarity	NPC470151
0.7317	Intermediate Similarity	NPC472944
0.7317	Intermediate Similarity	NPC472945
0.7312	Intermediate Similarity	NPC252253
0.7312	Intermediate Similarity	NPC3538
0.7312	Intermediate Similarity	NPC113500
0.7312	Intermediate Similarity	NPC477224
0.7312	Intermediate Similarity	NPC45959
0.7303	Intermediate Similarity	NPC474448
0.7303	Intermediate Similarity	NPC472745
0.7303	Intermediate Similarity	NPC477283
0.7292	Intermediate Similarity	NPC470030
0.7284	Intermediate Similarity	NPC127094
0.7284	Intermediate Similarity	NPC109457
0.7284	Intermediate Similarity	NPC195530
0.7284	Intermediate Similarity	NPC100586
0.7284	Intermediate Similarity	NPC157422
0.7283	Intermediate Similarity	NPC293609
0.7283	Intermediate Similarity	NPC149966
0.7283	Intermediate Similarity	NPC5632
0.7283	Intermediate Similarity	NPC36372
0.7273	Intermediate Similarity	NPC86238
0.7273	Intermediate Similarity	NPC476702
0.7263	Intermediate Similarity	NPC233649
0.7263	Intermediate Similarity	NPC470028
0.7262	Intermediate Similarity	NPC171658
0.7253	Intermediate Similarity	NPC102725
0.7253	Intermediate Similarity	NPC82955
0.7253	Intermediate Similarity	NPC473472
0.725	Intermediate Similarity	NPC241085
0.725	Intermediate Similarity	NPC299948
0.725	Intermediate Similarity	NPC470833
0.725	Intermediate Similarity	NPC470830
0.7241	Intermediate Similarity	NPC286719
0.7241	Intermediate Similarity	NPC477286
0.7237	Intermediate Similarity	NPC95804
0.7237	Intermediate Similarity	NPC185547
0.7229	Intermediate Similarity	NPC186851
0.7222	Intermediate Similarity	NPC202937
0.7222	Intermediate Similarity	NPC43912
0.7222	Intermediate Similarity	NPC140446
0.7209	Intermediate Similarity	NPC186588
0.7209	Intermediate Similarity	NPC7479
0.7209	Intermediate Similarity	NPC257296
0.7209	Intermediate Similarity	NPC248944
0.7204	Intermediate Similarity	NPC144790
0.7204	Intermediate Similarity	NPC88962
0.7204	Intermediate Similarity	NPC473726
0.7204	Intermediate Similarity	NPC149400
0.7204	Intermediate Similarity	NPC277774
0.72	Intermediate Similarity	NPC475968
0.7195	Intermediate Similarity	NPC473238
0.7195	Intermediate Similarity	NPC472341
0.7179	Intermediate Similarity	NPC243469
0.7179	Intermediate Similarity	NPC190827
0.7179	Intermediate Similarity	NPC475943
0.7176	Intermediate Similarity	NPC177343
0.7174	Intermediate Similarity	NPC470832
0.7174	Intermediate Similarity	NPC65550
0.7174	Intermediate Similarity	NPC223143
0.7162	Intermediate Similarity	NPC150713
0.7162	Intermediate Similarity	NPC119425
0.7162	Intermediate Similarity	NPC29976
0.716	Intermediate Similarity	NPC282454
0.716	Intermediate Similarity	NPC192192
0.7158	Intermediate Similarity	NPC139271
0.7158	Intermediate Similarity	NPC304011
0.7158	Intermediate Similarity	NPC116683
0.7143	Intermediate Similarity	NPC477614
0.7143	Intermediate Similarity	NPC136424
0.7143	Intermediate Similarity	NPC473436
0.7143	Intermediate Similarity	NPC249078
0.7143	Intermediate Similarity	NPC236099
0.7143	Intermediate Similarity	NPC209686
0.7143	Intermediate Similarity	NPC226491
0.7143	Intermediate Similarity	NPC107963

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC117137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	565
0.1-0.2	4785
0.2-0.3	2706
0.3-0.4	614
0.4-0.5	301
0.5-0.6	174
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7468	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6928	Phase 2
0.7021	Intermediate Similarity	NPD8171	Discontinued
0.6747	Remote Similarity	NPD4787	Phase 1
0.67	Remote Similarity	NPD1700	Approved
0.6625	Remote Similarity	NPD371	Approved
0.6404	Remote Similarity	NPD6115	Approved
0.6404	Remote Similarity	NPD6697	Approved
0.6404	Remote Similarity	NPD6118	Approved
0.6404	Remote Similarity	NPD6114	Approved
0.6346	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1811	Approved
0.6322	Remote Similarity	NPD1810	Approved
0.6292	Remote Similarity	NPD6116	Phase 1
0.6264	Remote Similarity	NPD7525	Registered
0.62	Remote Similarity	NPD7991	Discontinued
0.618	Remote Similarity	NPD6117	Approved
0.617	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4244	Approved
0.6163	Remote Similarity	NPD4245	Approved
0.6163	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7524	Approved
0.6092	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3702	Approved
0.6067	Remote Similarity	NPD3703	Phase 2
0.6064	Remote Similarity	NPD6695	Phase 3
0.6047	Remote Similarity	NPD3698	Phase 2
0.5977	Remote Similarity	NPD2686	Approved
0.5977	Remote Similarity	NPD2687	Approved
0.5977	Remote Similarity	NPD2254	Approved
0.5965	Remote Similarity	NPD7328	Approved
0.5965	Remote Similarity	NPD7327	Approved
0.5955	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD8033	Approved
0.5914	Remote Similarity	NPD4748	Discontinued
0.5913	Remote Similarity	NPD7516	Approved
0.5905	Remote Similarity	NPD4159	Approved
0.5872	Remote Similarity	NPD7320	Approved
0.5862	Remote Similarity	NPD8377	Approved
0.5862	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8294	Approved
0.5824	Remote Similarity	NPD6933	Approved
0.5816	Remote Similarity	NPD7750	Discontinued
0.5812	Remote Similarity	NPD8296	Approved
0.5812	Remote Similarity	NPD8335	Approved
0.5812	Remote Similarity	NPD8378	Approved
0.5812	Remote Similarity	NPD8380	Approved
0.5812	Remote Similarity	NPD8379	Approved
0.5811	Remote Similarity	NPD384	Approved
0.5811	Remote Similarity	NPD385	Approved
0.5795	Remote Similarity	NPD4789	Approved
0.578	Remote Similarity	NPD6412	Phase 2
0.5747	Remote Similarity	NPD6705	Phase 1
0.5747	Remote Similarity	NPD5360	Phase 3
0.5747	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6931	Approved
0.5745	Remote Similarity	NPD6930	Phase 2
0.5741	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.573	Remote Similarity	NPD5777	Approved
0.5729	Remote Similarity	NPD3669	Approved
0.5729	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6054	Approved
0.5726	Remote Similarity	NPD6059	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5688	Remote Similarity	NPD5739	Approved
0.5688	Remote Similarity	NPD6402	Approved
0.5688	Remote Similarity	NPD6008	Approved
0.5688	Remote Similarity	NPD6675	Approved
0.5688	Remote Similarity	NPD7128	Approved
0.5678	Remote Similarity	NPD7503	Approved
0.5676	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6053	Discontinued
0.566	Remote Similarity	NPD7640	Approved
0.566	Remote Similarity	NPD7639	Approved
0.5657	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6700	Approved
0.5644	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6929	Approved
0.563	Remote Similarity	NPD6370	Approved
0.5625	Remote Similarity	NPD4634	Approved
0.562	Remote Similarity	NPD7507	Approved
0.5619	Remote Similarity	NPD4755	Approved
0.5614	Remote Similarity	NPD4632	Approved
0.5614	Remote Similarity	NPD8133	Approved
0.5604	Remote Similarity	NPD6926	Approved
0.5604	Remote Similarity	NPD6924	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data